While I could likely write some decent landlord software, I'd rather see if someone else has done a better job than me.What, if any, software do you use to manage things?

Here in CA, using the standard CAR form, if you checked the box that financing is a contingency, you simply submit a written statement to the seller that you are terminating the agreement based on your right under the financing contingency ... assuming you are still within the contingency timeline.

I'd recommend running your returns by a CPA prior to submitting if you are self-preparing.

Confront tenant on the lease that their 'visitor' has been here longer than 14 days as agreed.Then hand her the application and teller that the visitor must submit this if he is going to stay.Once you have the info, then require that he too sign the lease if he expects to stay (vetting is optional, as you're after the personal data).Your 25% increase is questionable IMO as we rent units, not beds as in a hotel.

I'm looking at potentially submitting an offer on a multifamily home in Chicago.

Not to mention i could argue that investors who are agents and brokers have better access to deals, show properties for themselves, submit their own offers, save on closing costs ( which really adds up when your investing really takes off ), and market yourself to other investors and provide a second source of income when you help them find deals.

We currently use Propertyware and are not offered the ability to text from within the software.  

In order to submit an offer on the property I was looking at, she wanted me to sign a contract stating I would buy and sell only through her.   

However, the cost such as plumbing, ductwork, electrical, and lumber have to be capitalized and added to the basis of your house unless you meet any of these: 1)  The total cost is less than 2500. ( not just plumbing or electrical- total ) De minimis safe harborThe safe harbor applies to amounts paid during the tax year to acquire or produce what the regs call a “unit of property” (UOP), you must meet these requirements: (1) at the beginning of the tax year, the taxpayer has written accounting procedures treating as an expense for non-tax purposes amounts paid for property costing less than a specified dollar amount (which will be 2500 for you), or with an economic useful life of 12 months or less;.(2) the taxpayer treats the amount paid for the property as an expense on its books and records in accordance with its accounting procedures. ( do this on your bookkeeping software or whatever you utilize)(3) the amount paid for the UOP doesn't exceed $2,500. as substantiated by invoiceNote: The cost for the Unit of Property includes l additional costs (for example, delivery fees, installation services, or similar costs) if these additional costs are included on the same invoice with the tangible property. 

I can see the many ways that software can help his business run more smoothly, and I would like to propose an online software to help him out.